Aminoanthryl derivative substitution compound and organic electroluminescence device using the same

ABSTRACT

There is provided an aminoanthryl derivative substitution compound represented by the following general formula (1). The compound according to the present invention can provide an organic electroluminescence device showing an extremely pure luminescence hue, and an optical output with high efficiency, high luminance, and long life

CROSS REFERENCE TO RELATED APPLICATIONS

This is a submission to enter the national stage under 35 U.S.C. §371 ofPCT JP2004/009372.

TECHNICAL FIELD

The present invention relates to an organic electroluminescence device,and more particularly, to a device from which light is emitted byapplying an electric field on a thin film made of an organic compound.

BACKGROUND ART

An organic electroluminescence device is a device that includes a thinfilm made of a fluorescent organic compound between an anode and acathode, generates an exciton from the fluorescent compound by injectionof an electron and an electron hole (hereinafter, also simply referredto as a hole) from each electrode, and uses light to be radiated whenthe exciton returns to the ground state.

The study conducted by Eastman Kodak Company in 1987 (Appl. Phys. Lett.,51, p. 913, (1987)) reported light emission at about 1,000 cd/m² by anapplied voltage of about 10 V from a device including afunction-separated two-layer structure having an anode made of ITO and acathode made of magnesium-silver alloy where an aluminum quinolinolcomplex is used as each of an electron-transporting material and alight-emitting material and a triphenylamine derivative is used as ahole-transporting material. In this case, related patent documentsinclude U.S. Pat. Nos. 4,539,507, 4,720,432, and 4,885,211.

In addition, light emission at spectra ranging from ultraviolet throughinfrared is possible by changing the type of a fluorescent organicmaterial. Recently, various compounds have been studied actively anddescribed in many publications such as U.S. Pat. Nos. 5,151,629,5,409,783, and 5,382,477, Japanese Patent Application Laid-Open Nos.H02-247278, H03-255190, H05-202356, H09-202878, and H09-2275756.

Furthermore, in addition to the organic electroluminescence devicesusing low molecular weight materials as described above, an organicelectroluminescence device using a conjugated polymer has been reportedfrom the group of Cambridge University (Nature, 347, 539 (1990)). Thisreport has confirmed light emission from a monolayer by film formationwith polyphenylene vinylene (PPV) in a coating system. Patents relatedto an organic electroluminescence device using a conjugated polymerinclude U.S. Pat. Nos. 5,247,190, 5,514,878, and 5,672,678, JapanesePatent Application Laid-Open Nos. H04-145192, and H05-247460.

Recently, furthermore, an organic phosphorescence device using aniridium complex such as Ir (ppy)₃ (Appl. Phys. Lett., 75, 4 (1999)) hasbeen attracting attention and high luminous efficiency thereof has beenreported.

Recent advances in organic electroluminescence devices are remarkableand the characteristics thereof allow the formation of light-emittingdevices having high luminance with a low applied voltage, the variety ofemission wavelengths, high-speed responsiveness, low profile, andlightweight, suggesting the possibility for extensive uses. However,organic electroluminescence devices still involve many problems indurability, such as chronological changes by prolonged use, anddegradation with atmospheric gases containing oxygen, humidity, or thelike. When applications of organic electroluminescence devices tofull-color displays and so on are taken into consideration, under thepresent circumstances, blue-, green-, and red light-emissions withextended-life, high conversion rate, and high color purity have beendemanded.

Examples of the materials and organic electroluminescence devicescontaining anthracene rings include a phenyl anthracene derivativedisclosed in Japanese Patent Application Laid-Open No. H08-012600. Inparticular, when a phenyl anthracene derivative was used as a bluelight-emitting material or an electron-injection transporting material,the phenyl anthracene derivative supposedly allows the formation of agood organic film because of its low crystallinity. However, theluminous efficiency and durable life of the phenyl anthracene ring wereinsufficient in practical application.

An aminoanthracene derivative and a diaminoanthracene derivative havebeen disclosed as other examples in Japanese Patent ApplicationLaid-Open Nos. H09-157643 and H10-072579, respectively. In thedocuments, those materials supposedly generate green light-emission whenthey were used as light-emitting materials. However, devices preparedfrom those materials showed insufficient luminous efficiencies, andtheir durable lives were still insufficient in practical application.

Japanese Patent No. 3008897 discloses as another example a device usinga particular bianthryl compound as a light-emitting material, whichsupposedly generates light emission with high luminance. However, thepatent describes nothing about luminous efficiency and durable life.

Japanese Patent Application Laid-Open No. H11-008068 discloses as stillanother example a device using a particular anthracene compound havingan olefin site as a light-emitting material, which supposedly generateslight emission from yellow to red. However, the device showedinsufficient luminous efficiency in practical application.

Furthermore, Japanese Patent Application Laid-Open No. 2001-284050discloses as another example a device that contains an anthracenederivative having a particular structure, an electron-transportingcompound, and another fluorescent compound in a light-emitting mediumlayer. This device supposedly provides a red light-emitting device withimproved reliability. However, the device showed insufficient luminousefficiency in practical application. In addition, it was difficult toobtain blue light emission because of its device configuration.

DISCLOSURE OF THE INVENTION

The present invention has been made to solve the problems inherent inthe conventional technology and it is an object of the present inventionto provide an organic electroluminescence device exhibiting an extremelypure luminescence hue, and an optional output with high efficiency, highluminance, and long life. Another object of the present invention is toprovide an organic electroluminescence device which can be manufacturedwith ease at a relatively low cost.

The inventors of the present invention have made extensive study toattain the above objects, thereby completing the present invention.

That is, the present invention provides an aminoanthryl derivativesubstitution compound represented by the following general formula (1):

(wherein,

each of Y₁ to Y₄ is one selected from the group consisting of asubstituted or unsubstituted alkyl group, aralkyl group, aryl group, andheterocyclic group, Y₁ to Y₄ may be the same or different, and Y₁ andY₂, and Y₃ and Y₄ may bind to each other to form a ring;

each of Z₁ and Z₂ is one selected from the group consisting of a directbond, a substituted or unsubstituted alkylene group, alkenylene group,alkynylene group, aralkylene group, arylene group, and divalentheterocyclic group, and a divalent substituent having a coupling group,and Z₁ and Z₂ may be the same or different;

each of Z₃ and Z₄ is one selected from the group consisting of a directbond, a substituted or unsubstituted arylene group and divalentheterocyclic group, and a divalent substituent having a coupling group,and Z₃ and Z₄ may be the same or different;

X₁ is one selected from the group consisting of a hydrogen atom, a heavyhydrogen atom, a halogen atom, and a substituted or unsubstituted alkylgroup, aralkyl group, alkenyl group, alkynyl group, alkoxy group,sulfide group, aryl group, and heterocyclic group, and X₁ may be thesame or different;

R₁ is one selected from the group consisting of a hydrogen atom, a heavyhydrogen atom, a halogen atom, and a substituted or unsubstituted alkylgroup and alkoxy group, and R₁ may be the same or different;

each of R₂ and R₃ is one selected from the group consisting of ahydrogen atom, a heavy hydrogen atom, a halogen atom, and a substitutedor unsubstituted alkyl group, aryl group, alkoxy group, and amino group,and R₂ and R₃ may be the same or different; and

m is an integer of 0 to 3).

Furthermore, the present invention provides an aminoanthryl derivativesubstitution compound, in which X₁ is represented by the followinggeneral formula (2):

(wherein,

Z₅ is one selected from the group consisting of a direct bond, asubstituted or unsubstituted alkylene group, alkenylene group,alkynylene group, aralkylene group, arylene group, and divalentheterocyclic group, and a divalent substituent having a coupling group,and Z₅ may be the same or different;

X₂ is one selected from the group consisting of a hydrogen atom, a heavyhydrogen atom, a halogen atom, a substituted or unsubstituted alkylgroup, aralkyl group, alkenyl group, alkynyl group, alkoxy group,sulfide group, amino group, aryl group, and heterocyclic group, and X₂may be the same or different; and

R₄ is one selected from the group consisting of a hydrogen atom, a heavyhydrogen atom, a halogen atom, a substituted or unsubstituted alkylgroup, aryl group, alkoxy group, and amino group, and R₄ may be the sameor different).

Furthermore, the present invention provide an aminoanthryl derivativesubstitution compound, in which X₁ is represented by the followinggeneral formula (3):

(wherein,

each of Y₅ to Y₈ is one selected from the group consisting of asubstituted or unsubstituted alkyl group, aralkyl group, aryl group, andheterocyclic group, Y₅ to Y₈ may be the same or different, and Y₅ andY₆, and Y₇ and Y₈ may bind to each other to form a ring;

each of Z₆ to Z₈ is one selected from the group consisting of a directbond, a substituted or unsubstituted alkylene group, alkenylene group,alkynylene group, aralkylene group, arylene group, and divalentheterocyclic group, and a divalent substituent having a coupling group,and Z₆ to Z₈ may be the same or different;

each of Z₉ and Z₁₀ is one selected from the group consisting of a directbond, a substituted or unsubstituted arylene group and divalentheterocyclic group, and a divalent substituent having a coupling group,and Z₉ and Z₁₀ may be the same or different;

R₅ is one selected from the group consisting of a hydrogen atom, a heavyhydrogen atom, a halogen atom, and a substituted or unsubstituted alkylgroup and alkoxy group, and R₅ may be the same or different;

each of R₆ and R₇ is one selected from the group consisting of ahydrogen atom, a heavy hydrogen atom, a halogen atom, and a substitutedor unsubstituted alkyl group, aryl group, alkoxy group, and amino group,and R₆ and R₇ may be the same or different; and

n is an integer of 0 to 3).

BRIEF DESCRIPTION OF THE DRAWINGS

FIG. 1 is a cross sectional diagram illustrating an embodiment of anorganic electroluminescence device of the present invention;

FIG. 2 is a cross sectional diagram illustrating another embodiment ofthe organic electroluminescence device of the present invention;

FIG. 3 is a cross sectional diagram illustrating another embodiment ofthe organic electroluminescence device of the present invention;

FIG. 4 is a cross sectional diagram illustrating another embodiment ofthe organic electroluminescence device of the present invention; and

FIG. 5 is a cross sectional diagram illustrating another embodiment ofthe organic electroluminescence device of the present invention.

BEST MODE FOR CARRYING OUT THE INVENTION

The present invention provides an aminoanthryl derivative substitutioncompound represented by the following general formula (1):

(wherein,

each of Y₁ to Y₄ is one selected from the group consisting of asubstituted or unsubstituted alkyl group, aralkyl group, aryl group, andheterocyclic group, Y₁ to Y₄ may be the same or different, and Y₁ andY₂, and Y₃ and Y₄ may bind to each other to form a ring;

each of Z₁ and Z₂ is one selected from the group consisting of a directbond, a substituted or unsubstituted alkylene group, alkenylene group,alkynylene group, aralkylene group, arylene group, and divalentheterocyclic group, and a divalent substituent having a coupling group,and Z₁ and Z₂ may be the same or different;

each of Z₃ and Z₄ is one selected from the group consisting of a directbond, a substituted or unsubstituted arylene group and divalentheterocyclic group, and a divalent substituent having a coupling group,and Z₃ and Z₄ may be the same or different;

X₁ is one selected from the group consisting of a hydrogen atom, a heavyhydrogen atom, a halogen atom, and a substituted or unsubstituted alkylgroup, aralkyl group, alkenyl group, alkynyl group, alkoxy group,sulfide group, aryl group, and heterocyclic group, and X₁ may be thesame or different;

R₁ is one selected from the group consisting of a hydrogen atom, a heavyhydrogen atom, a halogen atom, and a substituted or unsubstituted alkylgroup and alkoxy group, and R₁ may be the same or different;

each of R₂ and R₃ is one selected from the group consisting of ahydrogen atom, a heavy hydrogen atom, a halogen atom, and a substitutedor unsubstituted alkyl group, aryl group, alkoxy group, and amino group,and R₂ and R₃ may be the same or different; and

m is an integer of 0 to 3).

Furthermore, the present invention provides an aminoanthryl derivativesubstitution compound, in which X₁ is represented by the followinggeneral formula (2):

(wherein,

Z₅ is one selected from the group consisting of a direct bond, asubstituted or unsubstituted alkylene group, alkenylene group,alkynylene group, aralkylene group, arylene group, and divalentheterocyclic group, and a divalent substituent having a coupling group,and Z₅ may be the same or different;

X₂ is one selected from the group consisting of a hydrogen atom, a heavyhydrogen atom, a halogen atom, a substituted or unsubstituted alkylgroup, aralkyl group, alkenyl group, alkynyl group, alkoxy group,sulfide group, amino group, aryl group, and heterocyclic group, and X₂may be the same or different; and

R₄ is one selected from the group consisting of a hydrogen atom, a heavyhydrogen atom, a halogen atom, a substituted or unsubstituted alkylgroup, aryl group, alkoxy group, and amino group, and R₄ may be the sameor different).

Furthermore, the present invention provide an aminoanthryl derivativesubstitution compound, in which X₁ is represented by the followinggeneral formula (3):

(wherein,

each of Y₅ to Y₈ is one selected from the group consisting of asubstituted or unsubstituted alkyl group, aralkyl group, aryl group, andheterocyclic group, Y₅ to Y₈ may be the same or different, and Y₅ andY₆, and Y₇ and Y₈ may bind to each other to form a ring;

each of Z₆ to Z₈ is one selected from the group consisting of a directbond, a substituted or unsubstituted alkylene group, alkenylene group,alkynylene group, aralkylene group, arylene group, and divalentheterocyclic group, and a divalent substituent having a coupling group,and Z₆ to Z₈ may be the same or different;

each of Z₉ and Z₁₀ is one selected from the group consisting of a directbond, a substituted or unsubstituted arylene group and divalentheterocyclic group, and a divalent substituent having a coupling group,and Z₉ and Z₁₀ may be the same or different;

R₅ is one selected from the group consisting of a hydrogen atom, a heavyhydrogen atom, a halogen atom, and a substituted or unsubstituted alkylgroup and alkoxy group, and R₅ may be the same or different;

each of R₆ and R₇ is one selected from the group consisting of ahydrogen atom, a heavy hydrogen atom, a halogen atom, and a substitutedor unsubstituted alkyl group, aryl group, alkoxy group, and amino group,and R₆ and R₇ may be the same or different; and

n is an integer of 0 to 3).

Furthermore, the present invention provides an aminoanthryl derivativesubstitution compound, in which the X₁ is an alkyl group.

Furthermore, the present invention provides an aminoanthryl derivativesubstitution compound, in which each of the Z₁ to Z₄ is a direct bond.

Furthermore, the present invention provides an aminoanthryl derivativesubstitution compound, in which at least one of the Y₁ to Y₄, Z₁ to Z₄,X₁, and R₁ to R₃ is a group containing a heavy hydrogen atom or a heavyhydrogen atom.

Furthermore, the present invention provides an aminoanthryl derivativesubstitution compound, in which at least one of the Y₁ to Y₄, Z₁ to Z₅,X₂, and R₁ to R₄ is a group containing a heavy hydrogen atom or a heavyhydrogen atom.

Furthermore, the present invention provides an aminoanthryl derivativesubstitution compound, in which at least one of the Y₁ to Y₈, Z₁ to Z₄,Z₆ to Z₁₀, R₁ to R₃, and R₅ to R₇ is a group containing a heavy hydrogenatom or a heavy hydrogen atom.

Furthermore, the present invention provides an aminoanthryl derivativesubstitution compound, in which at least one of the Y₁ to Y₄, Z₁ to Z₄,X₁, and R₁ to R₃ is a group containing a heavy hydrogen atom or a heavyhydrogen atom.

Furthermore, the present invention provides an aminoanthryl derivativesubstitution compound, in which at least one of the Y₁ to Y₄, X₁, and R₁to R₃ is a group containing a heavy hydrogen atom or a heavy hydrogenatom.

Furthermore, the present invention provides an organicelectroluminescence device including a pair of electrodes composed of ananode and a cathode at least one of which is transparent or translucent,and one or more organic compound layers sandwiched between the pair ofelectrodes, in which at least one of the organic compound layerscontains at least one kind of the aminoanthryl derivative substitutioncompounds.

Furthermore, the present invention provides an organicelectroluminescence device including a light-emitting layer, a pair ofelectrodes composed of an anode and a cathode at least one of which istransparent or translucent, and one or more organic compound layerssandwiched between the pair of electrodes, in which the light-emittinglayer contains at least one kind of the aminoanthryl derivativesubstitution compounds.

The compounds each represented by the general formula (1) and thecompounds each represented by the general formula (1) in which X₁ isrepresented by the general formula (2) or (3) can be predominantly usedas materials for an organic electroluminescence device, respectively.Each of the compounds may be solely used in a light-emitting layer for alight-emitting purpose or may be used for a dopant (guest) or hostmaterial to produce a device having high color purity, high luminousefficiency, and long life.

The compounds each represented by the general formula (1) and thecompounds each represented by the general formula (1) in which X₁ isrepresented by the general formula (2) or (3) contain at least twoanthryl groups as a luminescent unit with high luminous efficiency in abenzene ring core and the two anthryl groups are substituted by an aminogroup or an amino group with a coupling group. In introducing asubstituted amino group, luminescence colors of blue, green, and othercolors at longer wavelengths can be easily obtained by adjusting theHOMO/LUMO level of the material by the change of the substituent on theamino group (e.g., the HOMO/LUMO levels of Exemplified Compounds 27 and33 calculated with B3LYP/3-21G are −5.030/−1.877 and −4.805/−1.696,respectively). When the above compound is used as a dopant material, thedesired material can be easily designed and synthesized on the basis ofthe HOMO/LUMO level of the host material by making a prediction as tothe HOMO/LUMO level of the material by calculation with respect to thechange of the substituent on the anthryl group. In addition, the same isapplied when the above compound is used as a host material. Furthermore,the above compounds permit easy molecular design in consideration ofdifference in energy level with respect to the hole-transporting layerand the electron-transporting layer. An improvement in hole-transportingability can be expected from the substitution of an amino group. Inaddition, the amino group on the anthryl group can increase Tg (forexample, Exemplified Compound 28 has a Tg of 215° C.). As to the thermalcharacteristics of the device, a material having good film-formingability and thermal stability can be obtained when the compound adoptsthe form of a star-burst type dendritic molecule. The cohesion betweenmolecules can be prevented by introducing a steric hindrance group or afluorine atom having a large electronegativity which tends to cause anelectrostatic repulsion to a proximal molecule into the substituent onthe benzene ring core, the anthryl group, and the amino group, and suchintroduction can be particularly expected to extend the life of thedevice. In addition to the above consideration, the material of thepresent invention has considered the introduction of a molecule unitsubstituted with heavy hydrogen by an isotope effect in consideration ofinhibition of molecular vibration and thermal inactivation. The presentinvention has been achieved by performing molecular design on the basisof the above consideration.

Furthermore, when the compound is used as a dopant material, theconcentration of the dopant against the host material is 0.01% to 80%,preferably 1% to 40%. The dopant material may be distributed in a layermade of the host material uniformly or with a concentration gradient, ormay be partially distributed in a certain region of the host materiallayer to allow the layer to have a region containing no dopant material.

Hereinafter, the present invention will be described in detail.

Specific examples of the coupling group and the substituent in thegeneral formulae (1) to (3) described above are as follows:

Examples of a coupling group in each of the above general formulae (1)to (3) include, but not limited to, a substituted or unsubstitutedarylene group and divalent heterocyclic group.

Examples of a divalent substituent having a coupling group in each ofthe above general formulae (1) to (3) include, but not limited to, asubstituted or unsubstituted alkylene group, alkenylene group,alkynylene group, aralkylene group, and amino group, and a substitutedsilyl group, ether group, thioether group, and carbonyl group.

Examples of a substituted or unsubstituted alkyl group include, but notlimited to, a methyl group, a methyl-d1 group, a methyl-d3 group, anethyl group, an ethyl-d5 group, an n-propyl group, an n-butyl group., ann-pentyl group, an n-hexyl group, an n-heptyl group, an n-octyl group,an n-decyl group, an iso-propyl group, an iso-propyl-d7 group, aniso-butyl group, a sec-butyl group, a tert-butyl group, a tert-butyl-d9group, an iso-pentyl group, a neopentyl group, a tert-octyl group, afluoromethyl group, a difluoromethyl group, a trifluoromethyl group, a2-fluoroethyl group, a 2,2,2-trifluoroethyl group, a perfluoroethylgroup, a 3-fluoropropyl group, a perfluoropropyl group, a 4-fluorobutylgroup, a perfluorobutyl group, a 5-fluoropentyl group, a 6-fluorohexylgroup, a chloromethyl group, a trichloromethyl group, 2-chloroethylgroup, a 2,2,2-trichloroethyl group, a 4-chlorobutyl group, a5-chloropentyl group, a 6-chlorohexyl group, a bromomethyl group, a2-bromoethyl group, an iodomethyl group, a 2-iodoethyl group, ahydroxymethyl group, a hydroxyethyl group, a cyclopropyl group, acyclobutyl group, a cyclopentyl group, a cyclohexyl group, acyclopentylmethyl group, a cyclohexylmethyl group, a cyclohexylethylgroup, a 4-fluorocyclohexyl group, a norbornyl group, and an adamantylgroup.

Examples of a substituted or unsubstituted aralkyl group include, butnot limited to, a benzyl group, a 2-phenylethyl group, a2-phenylisopropyl group, a 1-naphthylmethyl group, a 2-naphthylmethylgroup, a 2-(1-napthyl)ethyl group, a 2-(2-napthyl)ethyl group, a9-anthrylmethyl group, a 2-(9-anthryl)ethyl group, a 2-fluorobenzylgroup, a 3-fluorobenzyl group, a 4-fluorobenzyl group, a 2-chlorobenzylgroup, a 3-chlorobenzyl group, a 4-chlorobenzyl group, a 2-bromobenzylgroup, a 3-bromobenzyl group, and a 4-bromobenzyl group.

Examples of a substituted or unsubstituted alkenyl group include, butnot limited to, a vinyl group, an allyl group (2-propenyl group), a1-propenyl group, an iso-propenyl group, a 1-butenyl group, a 2-butenylgroup, a 3-butenyl group, and a styryl group.

Examples of a substituted or unsubstituted alkynyl group include, butnot limited to, an acetylenyl group, a phenylacetylenyl group, and a1-propynyl group.

Examples of a substituted or unsubstituted aryl group include, but notlimited to, a phenyl group, a phenyl-d5 group, a 4-methylphenyl group, a4-methoxyphenyl group, a 4-ethylphenyl group, a 4-fluorophenyl group, a4-trifluorophenyl group, a 3,5-dimethylphenyl group, a 2,6-diethylphenylgroup, a mesityl group, a 4-tert-butylphenyl group, a ditolylaminophenylgroup, a biphenyl group, a terphenyl group, a 1-naphthyl group, a2-naphthyl group, a 1-naphthyl-d7 group, a 2-naphthyl-d7 group, a1-anthryl group, a 2-anthryl group, a 9-anthryl group, a 9-anthryl-d9group, a 2-phenanthryl group, a 3-phenanthryl group, a 4-phenanthrylgroup, a 9-phenanthryl group, a 9-phenanthryl-d9 group, a 1-pyrenylgroup, a 1-pyrenyl-d9 group, a 2-pyrenyl group, a 4-pyrenyl group, atetracenyl group, a pentacenyl group, a fluorenyl group, a triphenylenylgroup, and a perylenyl group.

Examples of a substituted or unsubstituted heterocyclic group include,but not limited to, a pyrrolyl group, a pyridyl group, a pyridyl-d5group, a bipyridyl group, a methylpyridyl group, a terpyrrolyl group, athienyl group, a thienyl-d4 group, a terthienyl group, a propylthienylgroup, a furyl group, a furyl-d4 group, an indolyl group, a1,10-phenanthroline group, a phenazinyl group, a quinolyl group, acarbazolyl group, an oxazolyl group, an-oxadiazolyl group, a thiazolylgroup, and a thiadiazolyl group.

Examples of a substituted or unsubstituted alkylene group include, butnot limited to, a methylene group, a methylene-d2 group, adifluoromethylene group, an ethylene group, an ethylene-d4 group, aperfluoroethylene group, a propylene group, an iso-propylene group, abutylene group, and a 2,2-dimethylpropylene group.

Examples of a substituted or unsubstituted aralkylene group include, butnot limited to, a benzylene group, a 2-phenylethylene group, a2-phenylisopropylene group, a 1-naphthylmethylene group, a2-naphthylmethylene group, a 9-anthrylmethylene group, a2-fluorobenzylene group, a 3-fluorobenzylene group, a 4-fluorobenzylenegroup, a 4-chlorobenzyl group, and a 4-bromobenyzlene group.

Examples of a substituted or unsubstituted alkenyl group include, butnot limited to, a vinylene group, an iso-propenylene group, a styrylenegroup, and a 1,2-diphenylvinylene group.

Examples of a substituted or unsubstituted alkynyl group include, butnot limited to, an acetylenylene group and a phenyl acetylenylene group.

Examples of a substituted or unsubstituted arylene group include, butnot limited to, a phenylene group, a biphenylene group, atetrafluorophenylene group, a dimethylphenylene group, a naphthylenegroup, an anthrylene group, a phenanthrylene group, a pyrenylene group,a tetracenylene group, a pentacenylene group, and a perylenylene group.

Examples of a substituted or unsubstituted divalent heterocyclic groupinclude, but not limited to, a furylene group, a pyrrorylene group, apyridilene group, a terpyridilene group, a thienylene group, aterthienylene group, an oxazolylene group, a thiazolylene group, and acarbazolylene group.

In a substituted or unsubstituted amino (—NR′R″) group, each of R′ andR″ is a hydrogen atom, a heavy hydrogen atom, the above substituted orunsubstituted alkyl group, aralkyl group, aryl group, or heterocyclicgroup, an alkylene group, alkenylene group, alkynylene group, aralkylenegroup, and amino group having a coupling group derived from asubstituted or unsubstituted arylene group, or divalent heterocyclicgroup, a substituted silyl group, ether group, thioether group, andcarbonyl group. Examples of the substituted or unsubstituted amino groupinclude, but not limited to, an amino group, an N-methylamino group, anN-ethylamino group, an N,N-dimethylamino group, an N,N-diethylaminogroup, an N-methyl-N-ethylamino group, an N-benzylamino group, anN-methyl-N-benzylamino group, an N,N-dibenzylamino group, an anilinogroup, an N,N-diphenylamino group, an N-phenyl-N-tolylamino group, anN,N-ditolylamino group, an N-methyl-N-phenylamino group, anN,N-dianisolylamino group, an N-mesityl-N-phenylamino group, anN,N-dimesitylamino group, an N-phenyl-N-(4-tert-butylphenyl)amino group,and an N-phenyl-N-(4-trifluoromethylphenyl)amino group.

Examples of a substituted or unsubstituted alkoxy group include: analkyloxy group and aralkyloxy group having the above substituted orunsubstituted alkyl group, or aralkyl group; and an aryloxy group havingthe above substituted or unsubstituted aryl group or heterocyclic group.Specific examples thereof include, but not limited to, a methoxy group,an ethoxy group, a propoxy group, a 2-ethyl-octyloxy group, a phenoxygroup, a 4-tert-butylphenoxy group, a benzyloxy group, and a thienyloxygroup.

Examples of a substituted or unsubstituted sulfide group include: analkylsulfide group or aralkylsulfide group having the above substitutedor unsubstituted alkyl group, or aralkyl group; and an arylsulfide grouphaving the above substituted or unsubstituted aryl group or heterocyclicgroup. Specific examples thereof include, but not limited to, amethylsulfide group, an ethylsulfide group, a phenylsulfide group, and a4-methylphenylsulfide group.

Examples of substituents which the above substituents and couplinggroups may additionally have include, but not limited to: a heavyhydrogen atom; alkyl groups such as a methyl group, an ethyl group, ann-propyl group, an n-butyl group, an n-pentyl group, an n-hexyl group,an n-heptyl group, an n-octyl group, an n-decyl group, an iso-propylgroup, an iso-butyl group, a sec-butyl group, a tert-butyl group, aniso-pentyl group, a neopentyl group, a tert-octyl group, a benzyl group,and a 2-phenylethyl group; alkoxy groups such as an aralkyl group, amethoxy group, an ethoxy group, a prdpoxy group, a 2-ethyl-octyloxygroup, a phenoxy group, a 4-tert-butylphenoxy group, and a benzyloxygroup; aryl groups such as a phenyl group, a 4-methylphenyl group, a4-ethylphenyl group, a 3-chlorophenyl group, a 3,5-dimethylphenyl group,a triphenylamino group, a biphenyl group, a terphenyl group, a naphthylgroup, an anthryl group, a phenanthryl group, and a pyrenyl group;heterocyclic groups such as a pyridyl group, a bipyridyl group, amethylpyridyl group, a thienyl group, a terthienyl group, apropylthienyl group, a furyl group, a quinolyl group, a carbazolylgroup, and an N-ethylcarbazolyl group; halogen groups; a hydroxyl group;a cyano group; and a nitro group.

Next, typical compounds represented by the general formulae (1) and (2)will be given. However, the present invention is not limited to thosecompounds.

Next, the organic electroluminescence device of the present inventionwill be described in detail.

The organic electroluminescence device of the present invention includesa pair of electrodes consisting of an anode and a cathode and one ormore organic-compound-containing layers. At least one of theorganic-compound-containing layers contains at least one kind of thecompounds represented by the general formula (1) or the general formula(1) in which X₁ is a compound represented by the general formula (2) or(3).

FIGS. 1 to 5 show preferable embodiments of the organicelectroluminescence device of the present invention. In each figure,reference numeral 1 denotes a substrate; 2, an anode; 3, alight-emitting layer; 4, a cathode; 5, a hole-transporting layer; 6, anelectron-transporting layer; 7, a hole-injection layer; and 8, ahole/exciton-blocking layer.

FIG. 1 is a cross sectional diagram that illustrates an organicelectroluminescence device according to an embodiment of the presentinvention. As shown in FIG. 1, the device is constructed by mounting theanode 2, the light-emitting layer 3, and the cathode 4 on the substrate1 in that order. The electroluminescence device used herein is useful inthe case where the device has a hole-transporting ability, anelectron-transporting ability, and a light-emitting ability by itself orwhere compounds having the respective properties are used incombination.

FIG. 2 is a cross sectional diagram that illustrates an organicelectroluminescence device according to another embodiment of thepresent invention. As shown in FIG. 2, the device is constructed bymounting the anode 2, the hole-transporting layer 5, theelectron-transporting layer 6, and the cathode 4 on the substrate 1 inthat order. In this case, a light-emitting material is useful when it isused in combination with merely a non-illuminant hole-transporting orelectron-transporting material using materials having hole-transportingability or electron-transporting ability or both of them in therespective layers. In this case, furthermore, the light-emitting layer 3is constructed of the hole-transporting layer 5 or theelectron-transporting layer 6.

FIG. 3 is a cross sectional diagram that illustrates an organicelectroluminescence device according to another embodiment of thepresent invention. As shown in FIG. 3, the device is constructed bymounting the anode 2, the hole-transporting layer 5, the light-emittinglayer 3, the electron-transporting layer 6, and the cathode 4 on thesubstrate 1 in that order. In this case, the carrier-transportingfunction and the light-emitting function are separated from each other.The device is used in combination with compounds havinghole-transporting ability, electron-transporting ability, andlight-emitting ability as appropriate, allowing a substantial increasein flexibility for material choice. Simultaneously, various kinds ofcompounds having different emission wavelengths can be used, allowing anincrease in variety of luminescence hue. Furthermore, an increase inluminous efficiency may be ensured by effectively closing each carrieror exciton in the middle light-emitting layer 3.

FIG. 4 is a cross sectional diagram that illustrates an organicelectroluminescence device according to another embodiment of thepresent invention. In FIG. 4, comparing with the device shown in FIG. 3,the device is constructed such that the hole-injection layer 7 isinserted in the layer structure on the anode 2 side (i.e., between thehole-transporting layer 5 and the anode 2). Therefore it is effective inimproving the close contact between the anode 2 and thehole-transporting layer 5 or improving the hole-injecting ability, sothat such a configuration of the device will be advantageous in loweringthe voltage of the device.

FIG. 5 is a cross sectional diagram that illustrates an organicelectroluminescence device according to another embodiment of thepresent invention. In FIG. 5, comparing with the device shown in FIG. 3,a layer for blocking the travel of a hole or exciton to the cathode 4(the hole/exciton-blocking layer 8) is inserted between thelight-emitting layer 3 and the electron-transporting layer 6. Using acompound having an extremely high ionization potential as thehole/exciton-blocking layer 8 allows the configuration of the device tobe effective in improving luminous efficiency.

However, all of the devices shown in FIGS. 1 to 5 are substantiallyfundamental device structures, so that the configuration of the organicelectroluminescence device using the compound of the present inventionis not limited to these examples. For instance, various kinds of layerstructures may be configured, such as the formation of an insulatinglayer on the boundary surface between an electrode and an organic layer,the formation of an adhesive or interference layer, or the formation ofa hole-transporting layer composed of two layers with differentionization potentials.

The compound used in the present invention, which is represented by thegeneral formula (1) or by the general formula (1) in which X₁ isrepresented by the general formula (2) or (3), can be used in each ofthe configurations of FIGS. 1 to 5.

In particular, an organic layer using the compound of the presentinvention is useful as a light-emitting layer, an electron-transportinglayer, or a hole-transporting layer. In addition, a layer formed by avacuum evaporation method, a solution coating method, or the like ishardly crystallized, so that the layer will be excellent in stabilityover time.

In the present invention, the compound represented by the generalformula (1) or by the general formula (1) in which X₁ is represented bythe general formula (2) or (3) is particularly used as a component ofthe light-emitting layer and may be used in combination with aconventionally known low molecular or polymer hole-transportingcompound, light-emitting compound, electron-transporting compound, orthe like as required.

Those compounds will be exemplified below.

A preferable hole-injection transporting material has excellent mobilityto make the injection of a hole from an anode easy and to transport theinjected hole to a light-emitting layer. Low molecular and highmolecular hole-injection transporting materials include a triarylaminederivative, a phenylene diamine derivative, a triazole derivative, anoxadiazole derivative, an imidazole derivative, a pyrazoline derivative,a pyrazolone derivative, an oxazole derivative, a fluorenone derivative,a hydrazone derivative, a stilbene derivative, a phthalocyaninederivative, a porphyrin derivative, and poly (vinylcarbazole), poly(silylene), poly (thiophene), and other conductive polymers. However,the material is not limited to those compounds. Hereinafter, some of thespecific examples of the material will be described.

Low Molecular Hole-injection Transporting Material

High Molecular Hole-injection Transporting Material

Examples of available materials which are mainly involved in alight-emitting function except the anthryl derivative substitutioncompound represented by the general formulae (1) and (2) include, butnot limited to: polycyclic condensed aromatic compounds (includingnaphthalene derivatives, phenanthrene derivatives, fluorene derivatives,pyrene derivatives, tetracene derivatives, coronene derivatives,chrysene derivatives, perylene derivatives, 9,10-diphenylanthracenederivatives, and rubrene); quinacridone derivatives; acridonederivatives; coumarin derivatives; pyran derivatives; Nile red; pyrazinederivatives; benzoimidazole derivatives; benzothiazole derivatives;benzoxazole derivatives; stilbene derivatives; organometallic complexes(including organic aluminum complexes such astris(8-quinolinolato)aluminum and organic beryllium complexes); andhigh-molecular derivatives such as poly(phenylene vinylene) derivatives,poly(fluorene) derivatives, poly(phenylene) derivatives, poly(thienylenevinylene) derivatives, and poly(acetylene) derivatives. Part of thespecific examples will be shown below.

Low Molecular Light-emitting Material

High Molecular Light-emitting Material

Metal Complex Light-emitting Material

The electron-injection transporting material may be optionally chosenfrom materials that simplify the injection of an electron from acathode, and that have a function of transporting the injected electroninto the light-emitting layer. The material is chosen by considering thebalance with the mobility of the carrier of the hole-transportingmaterial. Examples of the electron-injection transporting materialinclude, but not limited to, oxadiazole derivatives, oxazolederivatives, thiazole derivatives, thiadiazole derivatives, pyrazinederivatives, triazole derivatives, triazine derivatives, perylenederivatives, quinoline derivatives, quinoxaline derivatives, fluorenonederivatives, anthrone derivatives, phenanthroline derivatives, andorganometallic complexes. Part of the specific examples will be shownbelow.

In the organic electroluminescence devices according to the presentinvention, each of layers containing anthryl derivative groupsubstitution compounds represented by the general formulae (1) and (2)and layers containing other organic compounds is prepared as a thin filmgenerally by a vacuum evaporation method, an ionization depositionmethod, sputtering, plasma, or a conventional coating method (e.g., aspin coating, dipping, casting, LB, or inkjet method) in which thecompound is dissolved in an appropriate solvent. In the case of forminga film with the coating method, in particular, a film may be formedusing the compound in combination with an appropriate binder resin.

The above binder resins may be chosen from a wide variety of binderresins. Examples of the binder resin include, but not limited to,polyvinyl carbazole resins, polycarbonate resins, polyester resins,polyallylate resins, polystyrene resins, ABS resins, polybutadineresins, polyurethane resins, acrylic resins, methacrylic resins, butyralresins, polyvinyl acetal resins, polyamide resins, polyimide resins,polyethylene resins, polyethersulfone resins, diallyl phthalate resins,phenol resins, epoxy resins, silicone resins, polysulfone resins, andurea resins. Each of those may also be used singly. Alternatively, twoor more of them may be mixed as copolymers. Further, additives such asknown plasticizers, antioxidants, and ultraviolet absorbers may be usedin combination if required.

A desirable anode material has as large a work function as possible andexamples of such a material include: metal elements such as gold,platinum, silver, copper, nickel, palladium, cobalt, selenium, vanadium,and tungsten, and alloys thereof; and metal oxides such as tin oxide,zinc oxide, indium oxide, indium tin oxide (ITO) and indium zinc oxide.Further, conductive polymers such as polyaniline, polypyrrole,polythiophene, and polyphenylene sulfide may also be used. Each of thoseelectrode substances may be used singly. Alternatively, two or more ofthe substances may also be used in combination. Further, the anode mayadopt any one of a single layer construction and a multilayerconstruction.

On the other hand, a desirable cathode material has as small a workfunction as possible and examples of such a material include: metalelements such as lithium, sodium, potassium, calcium, magnesium,aluminum, indium, ruthenium, titanium, manganese, yttrium, silver, lead,tin, and chromium; and multiple alloys such as lithium-indium,sodium-potassium, magnesium-silver, aluminum-lithium,aluminum-magnesium, and magnesium-indium. Metal oxides such as indiumtin oxide (ITO) may also be used. Each of those electrode substances maybe used singly. Alternatively, two or more of the substances may also beused in combination. Further, the cathode may adopt any one of a singlelayer construction and a multilayer construction.

In addition, at least one of the anode and cathode is desirablytransparent or translucent.

Substrates which may be used in the present invention include: opaquesubstrates such as metallic substrates and ceramics substrates; andtransparent substrates such as glass, quartz, and plastic sheetsubstrates, but are not particularly limited to these materials. Inaddition, the substrate may have a color filter film, a fluorescentcolor converting film, a dielectric reflection film, or the like tocontrol colored light.

Furthermore, a protective layer or a sealing layer may be formed on theprepared device to prevent the device from contacting with oxygen,moisture, or the like. The protective layer may be a diamond thin film,a film made of an inorganic material such as metal oxide or metalnitride, or a polymer film made of a fluorine resin, polyparaxylene,polyethylene, silicone resin, polystyrene resin, or the like, or may bea photo-curing resin, or the like. Furthermore, the device itself may becovered with glass, an airtight film, metal, or the like and packagedwith an appropriate sealing resin.

Hereinafter, the present invention will be described more specificallywith reference to examples thereof, but the invention is not limited toeach of these examples.

EXAMPLE 1 Method of Producing Exemplified Compound No. 4

(Synthesis of Intermediate (II))

In a stream of nitrogen, 20.5 g (82 mmol) of 3,5-dibromotoluene and 73.1g (0.328 mol) of anthracene-9-boronic acid were dissolved in a deaeratedmixture solvent of 11 of toluene and 500 ml of ethanol, and the wholewas stirred. Then, a sodium carbonate aqueous solution prepared bydissolving 58 g of anhydrous sodium carbonate in 500 ml of water wasadded dropwise into the mixture. In a stream of nitrogen, the mixturewas stirred for 1 hour in an oil bath heated to 80° C., and then 9.47 g(8.2 mmol) of tetrakis(triphenylphosphine)palladium was added to themixture. The resultant mixture was heated and stirred for about 4 hoursin an oil bath heated to 80° C. The temperature of the reaction solutionwas returned to room temperature, and then cooled to 5° C. After that,the precipitated crystal was filtered. The crystal was dissolved in amixture solvent of toluene and hexane under heating, and purified bysilica gel column chromatography (toluene:hexane=1:3), resulting in 22 gof Intermediate (I).

A solution containing 15 g (33.7 mmol) of Intermediate (I) in 300 ml ofchloroform was cooled to 5° C. Then, 11.8 g (74.1 mmol) of brominedissolved in 70 ml of chloroform was gradually added dropwise into thesolution. After the dropwise addition, the mixture solution was stirredfor 2 hours at room temperature and then 300 ml of methanol was added tothe solution, followed by stirring the mixture for 2 hours at 5° C. Aprecipitate was filtered, and then dispersed and washed with acetone.Subsequently, the solution was re-cooled to 5° C. and a precipitate wasfiltered, resulting in 19.3 g of Intermediate (II).

(Synthesis of Exemplified Compound No. 4)

Under a nitrogen atmosphere, 458 mg (0.797 mmol) of bis(benzylideneacetone)palladium and 0.97 g (4.78 mmol) of tri-tert-butylphosphine weredissolved in 200 ml of xylene, and the whole was stirred for 1 hour atroom temperature. After 100 ml of xylene had been further added to thesolution, 3 g (4.98 mmol) of Intermediate (II) was added to the mixturein a stream of nitrogen, and the whole was stirred for 5 minutes in anoil bath heated to 50° C. 2.24 g (9.96 mmol) ofN-(4-t-butylphenyl)-N-phenylamine was dissolved in 50 ml of xylene, andthe resultant solution was added dropwise into the mixture.Subsequently, 1.43 g (14.9 mmol) of sodium tert-butoxide was added tothe mixture. The mixture was heated and stirred for about 5 hours in anoil bath heated to 130° C. After the temperature of the reactionsolution had been returned to room temperature, 100 ml of water wasadded to the reaction solution, and a water layer was separated from anorganic layer. Furthermore, the water layer was extracted with tolueneand ethyl acetate, and dried along with the organic layer by usingsodium sulfate. The solvent was distilled off and the residue waspurified by silica gel column chromatography (toluene:hexane=1:3),resulting in 2.9 g of Exemplified Compound No. 5.

EXAMPLE 2 Method of Producing Exemplified Compounds Nos. 35 and 60

(Synthesis of Intermediate (IV))

In a stream of nitrogen, 25.8 g (82 mmol) of tribromobenzene and 109.5 g(0.491 mol) of anthracene-9-boronic acid were dissolved in a deaeratedmixture solvent of 11 of toluene and 500 ml of ethanol and then thewhole was stirred. A sodium carbonate aqueous solution prepared bydissolving 86.8 g of anhydrous sodium carbonate in 800 ml of water wasadded dropwise into the solution. In a stream of nitrogen, the resultingmixture was stirred for 1 hour in an oil bath heated to 80° C., followedby the addition of 14.2 g (12.3 mmol) of tetrakis (triphenylphosphine)palladium. Then, the mixture was heated and stirred for about 4 hours inan oil bath heated to 80° C. The temperature of the reaction solutionwas returned to room temperature and further cooled to 5° C., followedby filtering the precipitated crystal out. The crystal was dissolved ina mixture solvent of chlorobenzene and heptane under heating and thenpurified by silica gel column chromatography(chlorobenzene:heptane=1:3), resulting in 25 g of Intermediate (III).

A solution containing 16.7 g (27.6 mmol) of Intermediate (III) in 300 mlof chloroform was cooled to 5° C. and 9.69 g (60.6 mmol) of brominedissolved in 70 ml of chloroform was gradually added dropwise into thesolution. After the dropwise addition, the solution was stirred for 2hours at room temperature. Subsequently, 300 ml of methanol was added tothe solution, and the whole was stirred for 2 hours at 5° C. Aprecipitate was filtered, dispersed and washed with acetone, thesolution was re-cooled to 5° C., and a precipitate was filtered,resulting in 21 g of Intermediate (V) as a mixture of monobromo,dibromo, and tribromo products (HPLC analysis, UV:area ratio, monobromoproduct:dibromo product:tribromo product=1:2.3:3.3).

(Synthesis of Exemplified Compounds Nos. 35 and 60)

Under a nitrogen atmosphere, 361 mg (0.627 mmol) of bis(benzylideneacetone)palladium and 0.76 g (3.76 mmol) of tri-tert-butylphosphine weredissolved in 230 ml of xylene, and the whole was stirred for 1 hour atroom temperature. After 100 ml of xylene had been further added to thesolution, 3 g (3.92 mmol, in terms of dibromo product) of Intermediate(IV) was added to the mixture in a stream of nitrogen, and the whole wasstirred for 5 minutes in an oil bath heated to 50° C. 2.24 g (7.84 mmol)of N-(2-(9,9-dimethylfluorenyl))-N-phenylamine was dissolved in 50 ml ofxylene, and the resultant solution was added dropwise into the mixture.Subsequently, 1.13 g (11.8 mmol) of sodium tert-butoxide was added tothe mixture. The mixture was heated and stirred for about 5 hours in anoil bath heated to 130° C. After the temperature of the reactionsolution had been returned to room temperature, 100 ml of water wasadded to the reaction solution, and a water layer was separated from anorganic layer. Furthermore, the water layer was extracted with tolueneand ethyl acetate, and dried along with the organic layer by usingsodium sulfate. The solvent was distilled off and the residue waspurified by silica gel column chromatography (toluene:hexane=1:3),resulting in 1.1 g of Exemplified Compound No. 35 and 2 g of ExemplifiedCompound No. 60.

EXAMPLE 3 Method of Producing Exemplified Compounds Nos. 51 and 58

(Synthesis of Intermediate (VI))

Intermediate (VI) was prepared as a mixture of monobromo, dibromo, andtribromo products in the same manner as in the synthesis of Intermediate(IV) (HPLC analysis, UV:area ratio, monobromo product dibromoproduct:tribromo product=1:2.5:3).

(Synthesis of Exemplified Compounds Nos. 51 and 58)

Under a nitrogen atmosphere, 180 mg (0.314 mmol) of bis(benzylideneacetone)palladium and 0.38 g (1.88 mmol) of tri-tert-butylphosphine weredissolved in 150 ml of xylene, and the whole was stirred for 1 hour atroom temperature. After 100 ml of xylene had been further added to thesolution, 1.55 g (1.96 mmol, in terms of dibromo product) ofIntermediate (VI) was added to the mixture in a stream of nitrogen, andthe whole was stirred for 5 minutes in an oil bath heated to 50° C. 0.70g (3.92 mmol) of diphenylamine-d10 was dissolved in 50 ml of xylene, andthe resultant solution was added dropwise into the mixture.Subsequently, 0.565 g (5.90 mmol) of sodium tert-butoxide was added tothe mixture. The mixture was heated and stirred for about 5 hours in anoil bath heated to 130° C. After the temperature of the reactionsolution had been returned to room temperature, 100 ml of water wasadded to the reaction solution, and a water layer was separated from anorganic layer. Furthermore, the water layer was extracted with tolueneand ethyl acetate, and dried along with the organic layer by usingsodium sulfate. The solvent was distilled off and the residue waspurified by silica gel column chromatography (toluene:hexane=1:3),resulting in 0.7 g of Exemplified Compound No. 51 and 0.75 g ofExemplified Compound No. 58.

EXAMPLE 4

An organic electroluminescence device having the structure shown in FIG.3 was prepared by the method described below.

On a glass substrate as a substrate 1, indium tin oxide (ITO) as ananode 2 was formed as a film with a film thickness of 120 nm by asputtering method and then used as a transparent conductive supportingsubstrate. Subsequently, the substrate was subjected to ultrasoniccleaning in acetone and isopropyl alcohol (IPA) in order. Next, thesubstrate was boiled and washed with IPA, followed by drying.Furthermore, the substrate was subjected to UV/ozone cleaning and usedas a transparent conductive supporting substrate.

Using a compound represented by the following structural formula as ahole-transporting material, a chloroform solution was prepared toconcentration of 0.5 wt %.

This solution was dropped onto the above ITO electrode. Subsequently,the ITO electrode was subjected to spin coating with the solution at arevolving speed of 500 rpm for 10 seconds at first and then 1,000 rpmfor 1 minute to form a thin film thereon. After that, the resulting thinfilm was placed in a vacuum oven at 80° C. and dried for 10 minutes tocompletely remove the solvent in the film. Consequently, ahole-transporting layer 5 thus obtained was 50 nm in thickness. Next,for a light-emitting layer 3, Exemplified Compound No. 27 describedabove was deposited on the hole-transporting layer 5. The resultinglight-emitting layer 3 was 20 nm in thickness. In this case, the degreeof vacuum at the time of deposition was 1.0×10⁻⁴ Pa and the filmformation was performed at a rate of 0.2 to 0.3 nm/second.

Furthermore, bathophenanthroline (BPhen) was formed as anelectron-transporting layer 6 to a thickness of 40 nm by a vacuumevaporation method. In this case, the degree of vacuum at the time ofdeposition was 1.0×10⁻⁴ Pa and the film formation was performed at arate of 0.2 to 0.3 nm/second.

Subsequently, using an aluminum-lithium alloy (lithium concentration=1atom %) as a deposition material, a metal layer film of 10 nm inthickness was formed on the organic layer mentioned above by a vacuumevaporation method, and successively an aluminum film of 150 nm inthickness was formed thereon by a vacuum evaporation method.Consequently, an organic electroluminescence device in which thealuminum-lithium alloy film was provided as an electron-injectionelectrode (cathode 4) was prepared. In this case, the degree of vacuumat the time of deposition was 1.0×10⁻⁴ Pa and the film formation wasperformed at a rate of 1.0 to 1.2 nm/second.

The resulting organic electroluminescence device was covered with aprotective glass and sealed with an acrylic resin binder in a dry airatmosphere to prevent the device from deteriorating with the adsorptionof moisture thereon.

From the device thus obtained, the inventors observed the emission ofgreen light with a light-emitting luminance of 290 cd/m² and a luminousefficiency of 6 lm/W at an applied voltage of 3 V when the ITO electrode(anode 2) was provided as a positive electrode and the Al—Li electrode(cathode 4) was provided as a negative electrode.

Furthermore, when the current density was kept at 3.0 mA/cm² and thevoltage was applied for 100 hours under a nitrogen atmosphere, the rateof luminance degradation after 100 hours was small, changing from-theinitial luminance of 280 cd/m² to a luminance of 270 cd/m².

COMPARATIVE EXAMPLE 1

An organic electroluminescence device was prepared in the same manner asin Example 4, except that the following comparative compound was usedinstead of Exemplified Compound No. 27, followed by subjecting thedevice to the same evaluation. The inventors observed the emission ofgreen light with a light-emitting luminance of 190 cd/m² and a luminousefficiency of 2 lm/W at an applied voltage of 3 V.

Furthermore, when the current density was kept at 3.0 mA/cm² and avoltage was applied for 100 hours under a nitrogen atmosphere, the rateof luminance degradation after 100 hours was large, changing from theinitial luminance of 180 cd/m² to a luminance of 80 cd/m².

EXAMPLES 5 TO 7

Organic electroluminescence devices were prepared in the same manner asin Example 4, except that the compounds listed in Table 1 were usedinstead of Exemplified Compound No. 27, followed by subjecting thedevices to the same evaluation. The results are shown in Table 1.

TABLE 1 Exemplified Applied Luminance Efficiency Example Compound No.voltage (V) (cd/m²) (lm/W) 5 8 3 270 6 6 29 3 320 7 7 49 3 340 8

EXAMPLE 8

An organic electroluminescence device having the structure shown in FIG.3 was prepared in the same manner as in Example 4, except that 2,9-bis(2-(9,9-dimethylfluorenyl))phenanthroline was used for anelectron-transporting layer 6 and Exemplified Compound No. 35 describedabove was deposited as a light-emitting layer 3.

From the device thus obtained, the inventors observed the emission ofgreen light with a light-emitting luminance of 340 cd/m² and a luminousefficiency of 8 lm/W at an applied voltage of 3 V when the ITO electrode(anode 2) was provided as a positive electrode and the Al—Li electrode(cathode 4) was provided as a negative electrode.

EXAMPLE 9

An organic electroluminescence device was prepared in the same manner asin Example 8, except that Exemplified Compound No. 6 described above wasdeposited as a light-emitting layer 3.

From the device thus obtained, the inventors observed the emission ofblue light with a light-emitting luminance of 210 cd/m² and a luminousefficiency of 3 lm/W at an applied voltage of 3 V when the ITO electrode(anode 2) was provided as a positive electrode and the Al—Li electrode(cathode 4) was provided as a negative electrode.

EXAMPLE 10

An organic electroluminescence device was prepared in the same manner asin Example 8, except that Exemplified Compound No. 11 described abovewas deposited as a light-emitting layer 3.

From the device thus obtained, the inventors observed the emission oforange light with a light-emitting luminance of 200 cd/m² and a luminousefficiency of 2 lm/W at an applied voltage of 3 V when the ITO electrode(anode 2) was provided as a positive electrode and the Al—Li electrode(cathode 4) was provided as a negative electrode.

EXAMPLES 11 TO 15

Just as in the case of Examples 9 and 10, organic electroluminescencedevices were prepared in the same manner as, in Example 8, except thatthe compounds listed in Table 2 were used, followed by subjecting thedevices to the same evaluation. The results are shown in Table 2.

TABLE 2 Exemplified Applied Luminance Efficiency Example Compound No.voltage (V) (cd/m²) (lm/W) 11 3 3 350 8 12 26 3 335 8 13 28 3 380 10 1430 3 240 4 15 45 3 400 11

EXAMPLE 16

A voltage was applied to the organic electroluminescence device preparedin Example 11 for 100 hours while the current density was kept at 3.0mA/cm² under a nitrogen atmosphere. Consequently, the rate of luminancedegradation after 100 hours was small, changing from the initialluminance of 345 cd/m² to a luminance of 325 cd/m².

EXAMPLE 17

A voltage was applied to the organic electroluminescence device preparedin Example 12 for 100 hours while the current density was kept at 3.0mA/cm² under a nitrogen atmosphere. Consequently, the rate of luminancedegradation after 100 hours was small, changing from the initialluminance of 340 cd/m² to a luminance of 330 cd/m².

COMPARATIVE EXAMPLE 2

An organic electroluminescence device was prepared in the same manner asin Example 8, except that the following unsubstituted comparativecompound was used for a light-emitting layer 3.

From the device thus obtained, the inventors observed the emission oflight with a light-emitting luminance of 240 cd/m² and a luminousefficiency of 0.2 lm/W at an applied voltage of 6 V when the ITOelectrode 2 was provided as a positive electrode and the Al—Li electrode4 was provided as a negative electrode.

From the above description with the embodiments and examples of thepresent invention, the aminoanthryl derivative substitution compound ofthe present invention represented by the general formula (1) and by thegeneral formula (1) in which X₁ is represented by the general formula(2) or (3) was developed on the basis of the design index as describedin the summary of the invention. Thus, the organic electroluminescencedevice using the materials of the invention allowed highly-efficientemission of light at a lower applied voltage. In addition, variousluminescent colors can be easily obtained by converting the substituentfrom one to another, and excellent durability can be also attained.

1. An aminoanthryl derivative substitution compound represented by thefollowing general formula (1):

wherein each of Y₁ to Y₄ is one selected from the group consisting of asubstituted or unsubstituted alkyl group, aralkyl group, aryl group, andheterocyclic group, Y₁ to Y₄ may be the same or different, and Y₁ andY_(2,) and Y₃ and Y₄ may bind to each other to form a ring; X₁ is oneselected from the group consisting of a hydrogen atom, a heavy hydrogenatom, a halogen atom, and a substituted or unsubstituted alkyl group,aralkyl group, alkenyl group, alkynyl group, alkoxy group, sulfidegroup, aryl group, and heterocyclic group; R₁ is one selected from thegroup consisting of a hydrogen atom, a heavy hydrogen atom, a halogenatom, and a substituted or unsubstituted alkyl group and alkoxy group,and R₁ may be the same or different; each of R₂ and R₃ is one selectedfrom the group consisting of a hydrogen atom, a heavy hydrogen atom, ahalogen atom, and a substituted or unsubstituted alkyl group, arylgroup, alkoxy group, and amino group, and R₂ and R₃ may be the same ordifferent; and m is an integer of 0 to
 3. 2. The aminoanthryl derivativesubstitution compound according to claim 1, wherein X₁ is represented bythe following general formula (2):

wherein X₂ is one selected from the group consisting of a hydrogen atom,a heavy hydrogen atom, a halogen atom, a substituted or unsubstitutedalkyl group, aralkyl group, alkenyl group, alkynyl group, alkoxy group,sulfide group, amino group, aryl group, and heterocyclic group; and R₄is one selected from the group consisting of a hydrogen atom, a heavyhydrogen atom, a halogen atom, a substituted or unsubstituted alkylgroup, aryl group, alkoxy group, and amino group, and R₄ may be the sameor different.
 3. The aminoanthryl derivative substitution compoundaccording to claim 1, wherein X₁ is an alkyl group.
 4. An organicelectroluminescence device comprising a pair of electrodes composed ofan anode and a cathode at least one of which is transparent ortranslucent, and one or more organic compound layers sandwiched betweenthe pair of electrodes, wherein at least one of the organic compoundlayers contains at least one of an aminoanthryl derivative substitutioncompound represented by the following general formula (1):

wherein each of Y₁ to Y₁ is one selected from the group consisting of asubstituted or unsubstituted alkyl group, aralkyl group, aryl group, andheterocyclic group, Y₁ to Y₄ may be the same or different, and Y₁ andY₉, and Y₃ and Y₄ may bind to each other to form a ring; X₁ is oneselected from the group consisting of a hydrogen atom, a heavy hydrogenatom, a halogen atom, and a substituted or unsubstituted alkyl group,aralkyl group, alkenyl group, alkynyl group, alkoxy group, sulfidegroup, aryl group, and heterocyclic group; R₁ is one selected from thegroup consisting of a hydrogen atom, a heavy hydrogen atom, a halogenatom, and a substituted or unsubstituted alkyl group and alkoxy group.and R₁ may be the same or different; each of R₂ and R₃ is one selectedfrom the group consisting of a hydrogen atom, a heavy hydrogen atom, ahalogen atom, and a substituted or unsubstituted alkyl group, arylgroup, alkoxy group, and amino group, and R₂ and R₃ may be the same ordifferent; and m is an integer of 0 to
 3. 5. An organicelectroluminescence device comprising a light-emitting layer, a pair ofelectrodes composed of an anode and a cathode at least one of which istransparent or translucent, and one or more organic compound layerssandwiched between the pair of electrodes, wherein the light-emittinglayer contains at least one of an aminoanthryl derivative substitutioncompound represented by the following general formula (1):

wherein each of Y₁ to Y₄ is one selected from the group consisting of asubstituted or unsubstituted alkyl group, aralkyl group, aryl group, andheterocyclic group, Y₁ to Y₄ may be the same or different, and Y₁ and Y₂and Y₃ and Y₁ may bind to each other to form a ring; X₁ is one selectedfrom the group consisting of a hydrogen atom, a heavy hydrogen atom, ahalogen atom, and a substituted or unsubstituted alkyl group, aralkylgroup, alkenyl group, alkynyl group, alkoxy group, sulfide group, arylgroup, and heterocyclic group; R₁ is one selected from the groupconsisting of a hydrogen atom, a heavy hydrogen atom, a halogen atom,and a substituted or unsubstituted alkyl group and alkoxy group, and R₁may be the same or different; each of R₂ and R₃ is one selected from thegroup consisting of a hydrogen atom, a heavy hydrogen atom, a halogenatom, and substituted or unsubstituted alkyl group, aryl group, alkoxygroup, and amino group, and R₂ and R₃ may be the same or different; andm is an integer of 0 to
 3. 6. The aminoanthryl derivative substitutioncompound according to claim 1, wherein the aminoanthryl derivativesubstitution compound is one selected from the following formulae:


7. The aminoanthryl derivative substitution compound according to claim6, wherein the aminoanthryl derivative substitution compound is selectedfrom the following formulae:


8. The aminoanthryl derivative substitution compound according to claim1, wherein the aminoanthryl derivative substitution compound is oneselected from the formulae:


9. The aminoanthryl derivative substitution compound according to claim8, wherein the aminoanthryl derivative substitution compound is oneselected from the following formulae: